9H-xanthene-9-carbonyl chloride → HCID 54046607, compound

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Reaction Steps

The title compound, white solid, m.p. 203-205° C. and MS: m/e=334.1 (M+) was prepared in accordance with the general method of example 44a from 5-propyl-oxazol-2-ylamine [Ber. 95,2419(1962)] and 9-xanthene-carboxylic acid chloride. 66b) The 5-propyl-oxazol-2-ylamine used in the above reaction was obtained as follows: 21.8 g (0.132 mol) of 2-bromobutyraldehyde [Chem.Ber., 70,1898(1937)] was dissolved in 67.5 ml of a 4:3 mixture of DMF and water. Urea, 8.77 g (0.145 mol) was added with stirring. The clear colorless solution was stirred for 16 h at 105° C. The resulting light yellow solution is cooled to 0° C. and 10 ml of 45% Sodium hydroxide solution was added. The solution turns dark yellow (pH 12). 100 ml of brine is added and the solution is extracted five times with 100 ml of a 9:1 mixture of methylene chloride and methanol. The combined organic phases were concentrated to yield 15.62 g of a reddish brown oil which was purified by flash chromatography on silica gel with a 9:1 mixture of methylene chloride and methanol as eluent. One obtains 6.2 g (0.049 mol, 37%) of 5-5-propyl-oxazol-2-ylamine as a yellow oil which was directly used without further purification, MS: m/e=126.1 (M+).

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